Single Electron Transfer in Nucleophilic Aliphatic Substitution. Evidence for Single Electron Transfer in the Reactions of 1-Halonorbornanes with Various Nucleophiles

A series of 1-halonorbornanes was used as a model system in reactions with severqal nucleophiles in order to determine the involvement of single electron transfer (SET) in nucleophilic aliphatic substitution in the absence of light. The 1-halonorbornanes were allowed to react with Me 3 Sn - , Ph 2 P - , AlH 4 - , N(iPr) 2 - , SPh - , and the 2-nitropropyl anion in ether solvents at room temperature to 0 o C. The results of product anlyses, the use of radical and radical anion trapping reagents, the results of deuterium labeling studies, and the nucleofugality effect support a SET mechanism for the reactions involving 1-iodonorbomane